#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/06/2210619.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2210619
loop_
_publ_author_name
'Li, Shu-Yan'
'Zhong, Ping'
'Hu, Mao-Lin'
'Li, Jin-Hai'
_publ_section_title
4-Bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-furyl)methyleneamino]-1H-pyrazole-3-carbonitrile
_journal_coeditor_code           HB2117
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4499
_journal_page_last               o4500
_journal_paper_doi               10.1107/S1600536806036877
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H6 Br Cl2 F3 N4 O'
_chemical_formula_moiety         'C16 H6 Br Cl2 F3 N4 O'
_chemical_formula_sum            'C16 H6 Br Cl2 F3 N4 O'
_chemical_formula_weight         478.06
_chemical_melting_point          432.5(5)
_chemical_name_systematic
;4-Bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-furyl)methyleneamino]-
1H-pyrazole-3-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.220(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.561(2)
_cell_length_b                   22.927(5)
_cell_length_c                   8.4322(19)
_cell_measurement_reflns_used    3479
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.68
_cell_measurement_theta_min      2.34
_cell_volume                     1837.5(7)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9676
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         2.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.571
_exptl_absorpt_correction_T_max  0.627
_exptl_absorpt_correction_T_min  0.366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.669
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0669P)²+1.8001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                2519
_reflns_number_total             3302
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2117.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '432-433' was changed to '432.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '432-433' was changed to '432.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1837.6(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210619
_cod_database_fobs_code          2210619
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Br Br1 0.22521(5) 0.72759(2) 0.92265(8) 0.0930(3) Uani d . 1
Cl Cl1 0.58296(14) 0.92319(6) 1.13007(13) 0.0774(4) Uani d . 1
Cl Cl2 0.45286(13) 0.89620(5) 0.49883(13) 0.0718(3) Uani d . 1
F F1 0.8423(4) 1.08118(16) 0.7604(5) 0.1312(14) Uani d . 1
F F2 0.8830(5) 1.0330(2) 0.5725(6) 0.1536(18) Uani d . 1
F F3 0.9813(4) 1.0133(3) 0.7968(10) 0.259(4) Uani d . 1
O O1 0.7600(3) 0.71005(12) 0.7911(3) 0.0630(7) Uani d . 1
N N1 0.4166(3) 0.87712(12) 0.8387(4) 0.0487(7) Uani d . 1
N N2 0.2870(3) 0.89978(13) 0.8499(4) 0.0558(8) Uani d . 1
N N3 -0.0535(4) 0.8609(2) 0.9115(5) 0.0847(12) Uani d . 1
N N4 0.5448(3) 0.78795(13) 0.8409(4) 0.0486(7) Uani d . 1
C C1 0.8680(6) 1.0261(2) 0.7261(8) 0.0876(15) Uani d . 1
C C2 0.7494(4) 0.98709(17) 0.7551(5) 0.0598(10) Uani d . 1
C C3 0.7247(4) 0.97558(17) 0.9099(5) 0.0609(11) Uani d . 1
H H3 0.7808 0.9922 0.9950 0.073 Uiso calc R 1
C C4 0.6155(4) 0.93901(16) 0.9364(5) 0.0529(9) Uani d . 1
C C5 0.5302(4) 0.91467(14) 0.8114(4) 0.0474(8) Uani d . 1
C C6 0.5577(4) 0.92709(15) 0.6569(5) 0.0524(9) Uani d . 1
C C7 0.6668(4) 0.96296(16) 0.6279(5) 0.0599(10) Uani d . 1
H H7 0.6847 0.9709 0.5239 0.072 Uiso calc R 1
C C8 0.4240(4) 0.81859(14) 0.8633(4) 0.0440(8) Uani d . 1
C C9 0.2904(4) 0.80250(15) 0.8911(5) 0.0506(9) Uani d . 1
C C10 0.2108(4) 0.85336(17) 0.8799(4) 0.0518(9) Uani d . 1
C C11 0.0634(4) 0.85882(18) 0.8968(5) 0.0610(10) Uani d . 1
C C12 0.5961(4) 0.75389(16) 0.9515(4) 0.0478(8) Uani d . 1
H H12 0.5558 0.7538 1.0471 0.057 Uiso calc R 1
C C13 0.7120(4) 0.71595(16) 0.9365(4) 0.0494(9) Uani d . 1
C C14 0.7864(4) 0.68091(18) 1.0433(5) 0.0615(10) Uani d . 1
H H14 0.7745 0.6770 1.1508 0.074 Uiso calc R 1
C C15 0.8852(4) 0.65151(19) 0.9608(6) 0.0696(12) Uani d . 1
H H15 0.9514 0.6244 1.0030 0.084 Uiso calc R 1
C C16 0.8654(5) 0.6700(2) 0.8112(6) 0.0735(12) Uani d . 1
H H16 0.9168 0.6572 0.7304 0.088 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C16 O1 C13 105.8(3) ?
N2 N1 C5 119.9(3) n
N2 N1 C8 113.6(3) n
C8 N1 C5 126.4(3) n
C10 N2 N1 103.3(3) n
C12 N4 C8 118.2(3) n
F3 C1 F1 107.5(6) n
F3 C1 F2 108.8(6) ?
F1 C1 F2 98.1(5) ?
F3 C1 C2 115.5(5) ?
F1 C1 C2 112.0(5) ?
F2 C1 C2 113.4(5) ?
C7 C2 C3 121.2(4) ?
C7 C2 C1 119.9(4) ?
C3 C2 C1 118.9(4) ?
C4 C3 C2 118.8(4) ?
C4 C3 H3 120.6 ?
C2 C3 H3 120.6 ?
C3 C4 C5 121.3(4) ?
C3 C4 Cl1 119.8(3) ?
C5 C4 Cl1 118.9(3) ?
C4 C5 C6 118.6(3) ?
C4 C5 N1 121.3(3) ?
C6 C5 N1 120.1(3) ?
C7 C6 C5 121.1(4) ?
C7 C6 Cl2 119.8(3) ?
C5 C6 Cl2 119.1(3) ?
C6 C7 C2 119.1(4) ?
C6 C7 H7 120.5 ?
C2 C7 H7 120.5 ?
N1 C8 C9 104.9(3) n
N1 C8 N4 120.7(3) n
C9 C8 N4 133.9(3) n
C8 C9 C10 106.0(3) n
C8 C9 Br1 127.3(3) n
C10 C9 Br1 126.6(3) n
N2 C10 C9 112.1(3) n
N2 C10 C11 120.8(3) n
C9 C10 C11 127.0(4) n
N3 C11 C10 177.3(5) ?
N4 C12 C13 123.4(3) n
N4 C12 H12 118.3 ?
C13 C12 H12 118.3 ?
C14 C13 O1 109.7(3) ?
C14 C13 C12 131.5(4) ?
O1 C13 C12 118.8(3) ?
C13 C14 C15 106.8(4) ?
C13 C14 H14 126.6 ?
C15 C14 H14 126.6 ?
C16 C15 C14 106.5(4) ?
C16 C15 H15 126.7 ?
C14 C15 H15 126.7 ?
C15 C16 O1 111.2(4) ?
C15 C16 H16 124.4 ?
O1 C16 H16 124.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C9 Br1 1.856(4) n
Cl1 C4 1.734(4) ?
Cl2 C6 1.730(4) ?
C1 F1 1.324(6) ?
C1 F2 1.328(7) ?
C1 F3 1.215(7) n
O1 C13 1.361(4) ?
O1 C16 1.361(5) ?
N1 N2 1.357(4) n
N1 C5 1.424(4) n
N1 C8 1.359(4) n
N2 C10 1.329(5) n
N3 C11 1.139(5) n
N4 C8 1.383(4) n
N4 C12 1.273(5) n
C1 C2 1.485(6) ?
C2 C7 1.377(6) ?
C2 C3 1.377(6) ?
C3 C4 1.376(6) ?
C3 H3 0.9300 ?
C4 C5 1.379(5) ?
C5 C6 1.386(5) ?
C6 C7 1.370(5) ?
C7 H7 0.9300 ?
C8 C9 1.373(5) n
C9 C10 1.390(5) n
C10 C11 1.437(5) n
C12 C13 1.425(5) ?
C12 H12 0.9300 ?
C13 C14 1.350(5) ?
C14 C15 1.405(6) ?
C14 H14 0.9300 ?
C15 C16 1.324(6) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655064
